Clayton, R and Davis, ML and Li, W and Fraser, W and Ramsden, CA (2017) Preparation of pyridine-stretched 2’-deoxyhypoxanthosine phosphoramidite. ARKIVOC, 2017 (3). 87 -104. ISSN 1551-7004

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Abstract

Pyridine-stretched 2(sic)-deoxyhypoxanthosine (strH) phosphoramidite was prepared in eight steps from Hoffer’s sugar (2(sic)-deoxy-3,5-di-O-(p-toluoyl)-alpha-D-erythro-pentofuranosyl chloride). Improved synthesis of the Hoffer sugar was achieved without need for distillation or chromatographic separation of intermediates, or use of gaseous HCl. Conditions were optimised to provide a key nitrile intermediate for the preparation of strH whereby the cesium salt of 4(5)-nitroimidazole was glycosylated using Hoffer’s sugar. The nitrile intermediate was also used to prepare pyridine-stretched 2(sic)-deoxyadenosine (strA) and pyridine-stretched 2(sic)-deoxy-2,6-diaminonebulamine (strD). Preliminary studies indicate that strH forms a stronger, size-expanded base pair with adenine compared with the Watson-Crick thymine-adenine base pair.

Item Type: Article
Additional Information: This is the final published version of the article (version of record). It first appeared online via ARKAT USA INC at http://dx.doi.org/10.3998/ark.5550190.p010.075 - please refer to any applicable terms of use of the publisher.
Uncontrolled Keywords: 5-Aminoimidazoles, Hoffer’s sugar, pyridine-stretched purines, hypoxanthosine, phosphoramidite
Subjects: Q Science > QD Chemistry
Depositing User: Symplectic
Date Deposited: 26 Sep 2017 12:53
Last Modified: 26 Sep 2017 12:53
URI: http://eprints.keele.ac.uk/id/eprint/4049

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